Pyrrolidine → HCID 58529481, compound

HRID 1972799Notes

Reaction equation

HRID 1972799 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1>CN(C=O)C.O>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][N:43]5[CH2:47][CH2:46][CH2:45][CH2:44]5)[CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 62657Potassium Phosphate, TribasicHCID 58529921HCID 58529921, compound

Product 1

HCID 58529481HCID 58529481, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from step 1 (60 mg, 0.13 mmol) was dissolved in 1 mL of DMF and K3PO4 (33 mg, 0.16 mmol) was added. The mixture was treated with pyrrolidine (0.15 mL, 1.55 mmol) and stirred for 1 hour. The mixture was diluted with water (10 mL) and stirred for 10 minutes. The precipitate was collected and purified by preparative HPLC eluting with 10%-90% acetonitrile/water (0.1% TFA) to provide 29 mg (54%) of the title compound.

Workup

  1. stirringstirred for 10 minutes
  2. customThe precipitate was collected
  3. custompurified by preparative HPLC
  4. washeluting with 10%-90% acetonitrile/water (0.1% TFA)

Sources & evidence

ORD record
ord-f6edc33443174641b941088fc927d24b
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…